Triethylamine → HCID 86662493, compound

HRID 1892036Notes

Reaction equation

HRID 1892036 reaction equation
C(OC1C=CC2C(=CC=CC=2)C=1C=NO)C1OC1.[CH2:19]([O:21][C:22]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]=1[CH:40]=[N:41][OH:42])=[O:23])[CH3:20].ClN1C(=O)CCC1=O.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:19]([O:21][C:22]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]=1[C:40]#[N+:41][O-:42])=[O:23])[CH3:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 86662489HCID 86662489, compoundHCID 86662492HCID 86662492, compound

Product 1

HCID 86662493HCID 86662493, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

As shown in Chemical Formula 4, 88.2 mg (0.268 mmol) of 2-[5-(ethoxycarbonyl)pentyloxy]-1-naphthoaldehyde oxime (7) was dissolved in 30 mL of chloroform and thereto, 38.2 mg (0.325 mmol) of N-chlorosuccinimide (NCS) and 48.3 mL (0.348 mmol) of triethylamine were added in an ice bath, followed by stirring the resultant reaction mixture for 10 minutes to effect the reaction. Then, the reaction solution was washed with 10 mL of pure water, and the organic phase was dried over MgSO4, followed by concentrating the solvent under reduced pressure to obtain 81.9 mg of 2-[5-(ethoxycarbonyl)pentyloxy]-1-naphthonitrile oxide C as a satisfactorily applicable crude product.

Workup

  1. customreaction mixture for 10 minutes
  2. customthe reaction
  3. washThen, the reaction solution was washed with 10 mL of pure water
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationby concentrating the solvent under reduced pressure

Sources & evidence

ORD record
ord-c02742ff4ae24ccfb4c0147b883f6c3b
Source dataset
uspto-grants-2013_08
Patent number
US08507611B2

Reaction notes

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